The research outline involves an investigation of the nature and properties of positively charged sp-hybridized carbon in organic molecules, i.e., vinyl carbonium ions. Experiments in the proposal are directed toward a study of the energetics, solvation, sterochemistry of substitution, and intimate structure of such ions. This investigation has significant theoretical importance; in addition positively charged carbon intermediates have been implicated in the biogenetic synthesis of steroids and terpenes, and vinyl cations may specifically intervene during the biogenesis of naturally occurring acetylene derivatives. The project should therefore contribute to a better understanding of important chemical processes occurring in organisms, and may also lead to more fruitful ways of duplicating these processes in the laboratory.